


Babysitting The Boys Next Door

by Tardisangel67



Category: Supernatural
Genre: Babysitting, Blowjobs, F/M, Other, Threesome, Threesome - F/M/M, low-key sorta incesteous, sam and dean bang the same chick, sam is 16 so kinda young
Language: English
Status: Completed
Published: 2018-01-29
Updated: 2018-01-29
Packaged: 2019-03-11 05:03:21
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 2,164
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13517136
Author URL: https://archiveofourown.org/users/Tardisangel67/pseuds/Tardisangel67
Summary: Despite being hunters and in their teens, Sam and Dean don't mind some company from Pamela late at night.They both have a crush on her, but there's no way she's into them right...?





	Babysitting The Boys Next Door

At eighteen years old, you wouldn’t think that Dean would need a babysitter when John went out of town.  
Dean was technically an adult, and had already stayed home with his brother while his dad went to deal with an out of town job numerous times. It’s just that knowing how dangerous the world is, Dean had told his father that he’d would rather have back up with him in case something unexpected pops up. It was true, he did want back up. He was a tough guy, but even he had to admit he was still young, but the real motive of his sudden need for company stemmed from more than fear. Their lifestyle didn’t really give them many occasions to make friends, so when he saw an opportunity to meet someone new, especially a girl his age he took it.  
His dad said he knew a friend who’s daughter kept children near by the place they have been staying lately, coincidentally. John had met her father during a hunt quite a few years ago. Since then, they have been as close of buddies as the hunting lifestyle permitted with it’s constant moves. They swapped information and tips about hunting different creatures, drank together, and were happy to lend each other a hand when they could. It was no surprise he had offered to have his daughter Pamela come over when John told him about Dean and Sam needing some surveillance.

Pamela happened to be just Dean’s type: dark hair, blue eyes, and a hell of a challenge. She was a few years older than him, in her mid twenties probably, and gave off that confident and experienced vibe that made Dean go weak.   
He spent the whole evening trying to hide his massive crush and boner, avoiding making either too obvious. Apparently his acting needed some touching up because once she had left, that evening, Sam came to see Dean in his room a sly smirk on his face.  
“You’re into her aren’t you Dean?” he asked already knowing the answer.  
Dean suddenly felt cornered. _Was he that obvious?_  
Sam sat down on Dean’s bed and looked down onto his older brother who stared back up at him blushing lightly. He hit him playfully on the shoulder.  
“C’mon Dean! It’s not a big deal. She’s hot. You dont have to be shy in front of me! You never are usually…” he teases his warm breath brushing over Dean’s face in the cold motel room.   
Dean rolls his eyes and gives in “Fine. Yeah, she’s pretty hot… but, she’d never go for a guy like me… have you seen me? I’m just an uneducated freak who can barely whip up a good conversation…” He shakes his head, pushing Sam away from him. “And why do you care? You’d be the last person I’d expect to want me to pursue my attractions… I mean you looked pretty interested too…” he trailed off  
Sam picks up where he had left off. “You think I would be jealous?”  
Dean nods hesitantly, implicitly asking how his brother would feel about it.  
Sam scoffed. “You really think that you and her hooking up would stop me getting a shot too ?” he glanced down at Dean “Please!” he rolled his eyes “You’re not _that_ good Dean…”  
Dean shifted away offended “And you think you are? You’re like twelve dude!”  
“Ha-ha, very funny Dean.” he answered sarcastically. “I’m almost sixteen, and, I’ve probably already had more experience than you…”  
Sam gets up and starts walking towards his own bed.  
“And I’m not shy.” he adds winking as he slides under the covers.  
Dean lays in his bed staring at the ceiling for a few seconds before realizing what Sam had just said.  
“Wait… no. You wouldn’t!” he protests.  
“Yes I would. May the best Winchester score !” he announces before turning his back to Dean. “Now get some sleep. You’re gonna need it to keep up with me tomorrow.”

The next evening Pamela was back, looking even more ravishing than before. Dean knew he had to make a move before Sam could, but he just didn’t know how to start. He must have looked worried because Pamela stopped to look him in the eye.  
“You okay, Dean? You look like someone told you there were werewolves right outside.” she joked while getting closer to him. She came to stand right by his side and sat a comforting hand on his shoulder. “Do you want me to check outside?”  
Her hand on his shoulder set Dean’s body aflame. He decided to gather all his courage up and go for it.  
“No.” he said a bit hurriedly “I’d much rather you stay here… with me” he sputtered.  
He put his hand on hers and tried his best to smile seductively.  
“Are you putting the moves on me Winchester?” she inquired a brow arched.  
Dean hesitated a second. Did she want him to be or not? He tried to notice any queues that would nudge him in the right direction.   
Her hand squeezed his shoulder gently and she hadn’t backed away, which was a pretty good sign. He leaned towards her and whispered near her ear.  
“You haven’t seen half of them yet Pam…”  
As he was planning his next move, he heard a loud clatter behind them and Pamela turned away. Before he had even turned around he already knew what was happening. Sam had staged an injury so she would go patch him up, that way he could show off his surprisingly well built body. It was with no surprise that he discovered his brother lain on the floor only wearing a bath towel around his waist. Pamela moved forward to help him up and Dean couldn’t tell her not to without sounding like a real dick.  
“Oh, are you all right Sam?” she inquired concerned  
Sam winced a little for the show before looking up at her with his puppy dog eyes.  
“I think I’m falling for you Pamela…” he announced with the most enticing voice he could muster.  
Pamela stared at him for a second before backing away. She crossed her arms and looked at both of them with a disapproving but amused gaze.  
“You two realize you’re the biggest dorks on earth right?! I mean…” she laughed “You,” she said nodding towards Dean “can barely get a sentence out around me. And you” she nodded again, this time towards Sam “are willing to brave the chance of injuring yourself to try and woo me with the lamest pickup line I’ve ever heard?” she sighed trying to remain serious “No wonder your dad hired me to babysit you. You’re a serious danger to yourselves !” She couldn’t resist laughing again.  
Both of the boys stared at her, already anxious, anticipating what she’d say next. They had made such fools of themselves. There was no way they could catch up now. Sam got up and secured the towel stepping away in shame, while Dean suddenly became fascinated with the ceiling fan.  
“Boy, you guys are dorks… but I have to say, you’re cute as can be.” she confessed   
They both stared at her surprised at the turn this was taking.  
“You both have mommy and daddy issues written all over you, but I’m not gonna lie, something about that really works for me.” She stopped and looked them both in the eyes. “So are we doing this or not?” she asked smiling at each of them.  
The brothers exchanged a quick confused glance.  
“O-Of course. Yeah !” Sam blurted out.  
“Definitely!” Dean said enthusiastically.

Pamela flashed a flirty smile at them before turning away and speaking to them over her shoulder.  
“Well, I think I might just go freshen up a little.” She winked at them. “I’ll be right back.”  
She then locked herself into the bathroom and turned on the tap.  
Sam looked confusedly at Dean who answered his implicit question.  
“I think it’s girl talk for _get ready for sex_. I’d have thought you’d know that Casanova !” he teased “So, I guess we should get naked?” he proposed.  
Sam looked uneasy. “Like right here, in front of each other?”  
Dean shrugged “I guess.” He tugged his shirt over his head. “Don’t worry Sammy! I’ve already seen you in the nude. You have nothing to be ashamed of!” he reassured him.  
Dean’s encouragement and relaxed demeanor convinced Sam to go with it and he started undressing.  
They had just finished undressing when the water stopped in the bathroom. They heard the door unlock, and out stepped Pamela. She was wearing a mismatched underwear and bra set, but _damn_ , something about the spontaneity of it was enticing.  
She strutted up to the two brothers, until she was pressed between them and, got on the tip of her toes to whisper in their ears.  
“Let’s take this party to the bed.”  
The three of them then proceeded to the other corner of the room where the bed was positioned. Pamela sat down, the Winchesters facing her. She looks them over, deciding how they were going to work things out.  
Dean stared expectantly at her, and hesitantly asked “Umm.. How does this usually go?”  
She stared back at him shocked for an instant before laughing “Do you think that I do this often? That I just go around having casual threesomes?” she paused to laugh again “Really? I’m a beautician and part-time babysitter. When I’m not bleaching someone’s upper lip, I’m cleaning up a child’s mess. I rarely have much time to make any of my own…”  
By the time she finished her sentence, she was smiling knowingly. She had had an idea. “I guess we can just try something?” she offered.  
Sam and Dean nodded. She took Dean’s hand and put it on her hip, sliding his fingers under the hem of her underwear.  
“How about you get me out of these and get started?”  
Dean was happy to comply. He slid her panties down while he kissed her.  
She broke away from the kiss to look over to Sam.  
“Get over here Sammy!” she called the younger brother.  
Sam stepped forwards until he was touching her.  
“Have you ever gotten a blowjob, Sam?”  
Sam shook his head, a curious look in his eyes.  
“Well today’s your lucky day!” she winked at him before pushing him onto the bed and undoing his belt.  
Dean stood behind her watching his brother get all her attention. Once she had freed Sam from his pants and underwear, Pam turned to look back at Dean.  
“Don’t just stand there Dean! Show me you’re a Winchester like your daddy.”  
Dean registered her mentioning his father, but chose to ignore it for now. He grabbed a condom from the bedside and rolled it on. Dean lined up behind her and slid in. He stayed put for a moment before moving slowly, earning a moan from Pamela, which made Sam gasp in turn. Dean tentatively tried to move again trying to find a good rhythm which would have all of them moaning in sync. It only took a few minor adjustments, and, not long after he heard Sam cry out as the perfect rhythm drove him to completion. Pamela and him weren’t going to tease him for coming so quick, since they didn’t last much longer. Sam’s disheveled state struck something in Pamela causing her to tense up with the force of her orgasm, pushing Dean over the edge as well.  
Pamela sat up, and slid off of both Winchesters. She laid down on the bed, catching her breath. After a few minutes of silence, she took a deep breath and got up off the bed. The brothers looked at her.  
“Where are you going Pam?” Sam asked wide eyed.  
She smiled a bit. “I’m just going to go wash off. You really have some bad abandonment issues, boy…” She blew them a kiss. “I’ll be right back. Mind if I borrow one of your shirts?”  
“Nah, go ahead Pam.” Dean said.  
The door locked and the tap turns on again. The two brothers lay in silence, not sure what to say. Sam breaks the silence with a laugh.  
“Well I guess we both scored this time…” he comments “but don’t be mistaken, I’m the one she’s into. I mean she’s the one who offered to go down on me…” he jokes. Dean shoves him in a friendly manner.  
“Yeah, right… She just did that because she didn’t trust you could get the job done for her.” Dean retaliates.  
Sam returns his brotherly push with a scoff. “Dream on!”  
Dean laughs. “Bitch.”  
“Jerk.” Sam answers.  
Pamela comes back into the room to see the two of them squabbling. She stood at the bottom of the bed, in Dean’s oversized tee, with her arms crossed.  
“No need to fight boys… I promise there’s enough of me for both of you !” she scolds them lovingly and gets back into the bed between them.


End file.
